Biomedical subjects
Publications and source records attributed to A Kreutzberger.
Condensation of N-(2-hydroxyethyl)-N-methylguanidine-sulfate (1) with the beta-diketones 4a-e bearing 1-aryl substituents leads to the bioisosteric 2-[(2-hydroxyethyl)-methylamino]-6-arylpyrimidines 5a-e. Compounds 5a-c exhibit significant antimycotic in vivo and in vitro activities.
Partially introduction of the biguanide structure into heterocyclic systems leads to various substituted 2-guanidino-4(3H)-chinazolinones. The compounds exhibit significant antimycotic and gyrase-inhibiting activities.
The reactions of 2,4-dichloro-6-diethylamino-1,3,5-triazine (1) with the secondary amines 2a-g lead to the diamino-1,3,5-triazines 3a-e and the melamines 4a and 4b. The structures of the reaction products were established spectroscopically (IR, 1H-NMR, and MS).
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The nucleophilic substitution of one chlorine atom in cyanuric chloride (1) by piperidine derivatives (2a-c) leads to the 6-substituted 2,4-dichloro-1,3,5-triazines (3a-c). Reaction of 1 with piperazine derivatives (4a-c) yields the substituted 2,4-dichloro-6-(1-piperazinyl)-1,3,5-triazines (5a-c). Structures of type 3 and 5 may be characterized by the spectroscopic data. In the mass spectra, the degradation of 3c leading to the base peak comprises the cleavage into a 2,4-dichlorotriazinyl radical and a 3,4-dihydroquinolinium ion m/e 132. Strong activity is exhibited by 5a and 5b towards Trichomonas vaginalis. Moreover, 5a displays strong antimycotic activity towards Trichophyton mentagrophytes, Trichophyton rubrum, and Microsporum canis. Additionally, 5a and 5b are capable of exerting very strong anthelminthic activity towards Caenorhabditis elegans.
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The nucleophilic substitution of one chlorine atom in 2,4-dichloro-6-(dihexylamino)-1,3,5-triazine (1) by primary (2a-b) or secondary (2c) amines leads to the aliphatically substituted chloro-dihexylamino-1,3,5-triazines (3a-c) Structures of type 3 may be characterized by the spectroscopic data. In the mass spectra, the complete degradation of the alkyl groupings is striking and manifested in a series of consecutive peaks with differences of 14 between each other. Antiviral activity is exhibited by 3a through an inhibitory effect towards vaccinia virus and by 3b as interferon inductor towards encephalomyocarditis virus. Moreover, 3a and 3b exhibit a strong activity towards Trichomonas vaginalis. Additionally, 3a is capable of exerting temperature lowering and anthelminthic effects.
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